Lithium Hydroxide → 4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

HRID 14310

Reaktionsgleichung

Reaktionsgleichung von HRID 14310
[CH:1]1([C:11]([O:13]C)=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.CO.O>[CH3:10][O:9][C:7]([CH:4]1[CH2:5][CH2:6][CH:1]([C:11]([OH:13])=[O:12])[CH2:2][CH2:3]1)=[O:8]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 7198Dimethyl 1,4-cyclohexanedicarboxylate

Produkt 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a stirred solution of dimethyl cyclohexane-1,4-dicarboxylate (10.2 g, 51 mmol) in a mixture of 2:1:1 tetrahydrofuran/methanol/water (52 mL) was added lithium hydroxide (2.13 g, 51 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was partitioned between diethyl ether and water. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid, and the precipitate collected, and dried under vacuum to afford 4-(methoxycarbonyl)cyclohexanecarboxylic acid (7.4 g): 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 2.33-2.27 (m, 2H), 2.11-2.06 (m, 4H), 1.50-1.43 (m, 4H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between diethyl ether and water
  3. customthe precipitate collected
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0a58eacd02b5468d880f03d8c475fcf6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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